Sugarplum Style Tip | How to Wear Ankle Boots with Skinny Jeans

Happy almost-Friday, friends, and cheers to the long weekend ahead! We have one last (belated) Christmas celebration, and then we’re headed to the lake to usher in the new year with family.

It’s hard to believe another year has come and gone, and I’ve managed to create over 200 posts here! I’ll be recapping all my favorites next week, but thought I’d finish out this year with one of my most-asked style questions this time of year…how do you wear ankle boots with skinny jeans?!

And as is true with most of my Sugarplum Style Tips…my biggest advice is not to overthink it! There really are no rules when it comes to boots and jeans, or how you cuff them. It’s mostly a preference thing. I’ve styled two basic outfits to share my tips, starting with this favorite relaxed cowlneck (currently 40% off!).

Cowlneck Sweater (40% off!) | Jeans | Ankle Booties | Tassel Earrings | Belt | Sunglasses

Cowlneck Sweater (40% off!) | Jeans | Tassel Earrings | Belt | Sunglasses | Cuff Bracelet

And while there are no right or wrong ways for cuffing, some are definitely more flattering than others! When it comes to ankle boots (basically any boot but knee-high or over-the-knee) and skinny jeans, I’m not a fan of tucking your jeans in the boots, or pulling them over the top of the boot. Leave those looks to tall boots and bootcut jeans.

The goal is to see at least a sliver of skin between the boot and hem of the jean.

Depending on the length of your jeans, that likely requires some sort of cuff…and there are several to choose from, depending on the look and style you prefer.

*The Slouchy Cuff*

Most skinny jeans are tight enough to hug the leg, so you can do a single cuff and let the rest of the length scrunch around the ankle. This look is casual and effortless.

*The Wide Cuff*

Fold the excess length up in a single wide cuff, making sure the cuffs are fairly even on both legs. This looks best on tall or leggy girls, as it can visually shorten the legs.

*The Messy Roll*

Fold the jeans up in a single, wide cuff, then fold them up again so the cuff is smaller, but the hem of the jeans are still exposed. This is how I cuff my jeans 99% of the time.

*The Double Roll*

Just as the name suggests, simply fold the hem up twice, creating a clean, even cuff. This style is is a more tailored look.

If you prefer a simpler method, or don’t like to cuff at all, choose jeans with a shorter inseam, or have them altered to ankle-length. Most of my jeans are a shorter inseam like these, and just require a simple, messy cuff.

Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Sunglasses | Leopard Belt | Earrings

Mockneck Sweater (under$50!) | Distressed Jeans | Leopard Belt

Mockneck Sweater (under$50!) | Distressed Jeans | Ankle Booties | Leopard Belt

I hope this post was helpful and gave you some fresh ideas for cuffing your jeans with ankle boots. What method do you use most? See more of my Sugarplum Style Tips here.

I hope your holiday has been joyful and merry, and you have a safe, healthy and blessed New Year! I’m so thankful for each of you, and excited to continue this journey together! See you next week for a look back at 2017, and my favorite posts of the year.

Until then, don’t forget about the amazing Half-Yearly Sale at Nordstrom, and the unbelievable prices on a huge selection of in-season staples, including this long cardigan, these buffalo plaid lounge pants, Ugg slippers, and all these booties! Happy New Year, lovebugs!

{Fave Ankle Booties (all on sale!)}

{Huge Sale Alert on These Wardrobe Faves}


*Photos by the darling & talented Mary Summers. This post created in collaboration with Nordstrom, but all styling, tips and bowleggedness are my own. Thank you for supporting Hi Sugarplum sponsors!*



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